JPH043375B2 - - Google Patents
Info
- Publication number
- JPH043375B2 JPH043375B2 JP5698684A JP5698684A JPH043375B2 JP H043375 B2 JPH043375 B2 JP H043375B2 JP 5698684 A JP5698684 A JP 5698684A JP 5698684 A JP5698684 A JP 5698684A JP H043375 B2 JPH043375 B2 JP H043375B2
- Authority
- JP
- Japan
- Prior art keywords
- benzyl ester
- benzoic acid
- acid benzyl
- useful
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- STOLHTSXPDNJJX-UHFFFAOYSA-N (4-phenylmethoxycarbonylphenyl) 4-acetyloxybenzoate Chemical compound C1=CC(OC(=O)C)=CC=C1C(=O)OC1=CC=C(C(=O)OCC=2C=CC=CC=2)C=C1 STOLHTSXPDNJJX-UHFFFAOYSA-N 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- CGEOYYBCLBIBLG-UHFFFAOYSA-N (4-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C(Cl)=O)C=C1 CGEOYYBCLBIBLG-UHFFFAOYSA-N 0.000 description 2
- LQNKJAVVNUOIIB-UHFFFAOYSA-N (4-phenylmethoxycarbonylphenyl) 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OC1=CC=C(C(=O)OCC=2C=CC=CC=2)C=C1 LQNKJAVVNUOIIB-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- GDBUZIKSJGRBJP-UHFFFAOYSA-N 4-acetoxy benzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C=C1 GDBUZIKSJGRBJP-UHFFFAOYSA-N 0.000 description 1
- MOZDKDIOPSPTBH-UHFFFAOYSA-N Benzyl parahydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OCC1=CC=CC=C1 MOZDKDIOPSPTBH-UHFFFAOYSA-N 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、式
で表わされる新規なｐ−（ｐ−アセトオキシベン
ゾイルオキシ）安息香酸ベンジルエステルに関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the formula The present invention relates to a novel p-(p-acetoxybenzoyloxy)benzoic acid benzyl ester represented by:
本発明の式（）の化合物は、たとえば、ｐ−
アセトキシ安息香酸クロライドとｐ−ヒドロキシ
安息香酸ベンジルエステルとを、適当な溶媒（ベ
ンゼン、トルエン、キシレン、クロロホルムな
ど）中、アミン類の存在下に加熱反応させること
により、ｐ−（ｐ−アセトオキシベンゾイルオキ
シ）安息香酸ベンジルエステルを得ることができ
る。 The compound of formula () of the present invention is, for example, p-
P-(p-acetoxybenzoyl Oxy)benzoic acid benzyl ester can be obtained.
本発明化合物は、衛生害虫、たとえばゴキブリ
や白蟻などに対して忌避作用を有し、従つてたと
えば、害虫忌避剤として有用なｐ−（ｐ−ヒドロ
キシベンゾイルオキシ）安息香酸ベンジルエステ
ルの重要な中間体として有用である。また、前記
ｐ−（ｐ−ヒドロキシベンゾイルオキシ）安息香
酸ベンジルエステルは殺菌作用を有し、工業用殺
菌剤としても有用であり、しかも感熱紙用顕色剤
として有用な化合物である。 The compound of the present invention has a repellent effect on sanitary pests such as cockroaches and termites, and is therefore an important intermediate for p-(p-hydroxybenzoyloxy)benzoic acid benzyl ester useful as a pest repellent. It is useful as Furthermore, the p-(p-hydroxybenzoyloxy)benzoic acid benzyl ester has a bactericidal effect and is useful as an industrial bactericide, and is also a compound useful as a color developer for thermal paper.
実施例 １
冷却管、温度計を付した200ml四頚フラスコに
ｐ−アセトキシ安息香酸36ｇおよびチオニルクロ
ライド71.4ｇを仕込み、50℃で４時間反応させ
る。減圧下に過剰のチオニルクロライドを留去す
ると、ｐ−アセトキシ安息香酸クロライドが得ら
れる。次に、同様に冷却管、温度計、滴下ロート
を付した300ml四頚フラスコに、ｐ−ヒドロキシ
安息香酸ベンジルエステル45.7ｇ、トリエチルア
ミン20.2ｇおよびトルエン100mlを仕込む。30℃
に昇温し、ｐ−アセトキシ安息香酸クロライド
39.7ｇをトルエン50ｇに溶解し、１時間で滴下
し、その後50℃で30分間反応させる。冷後、反応
液を水50mlで３回洗浄し、減圧下に溶媒を留去す
る。残渣をメタノールから再結晶すると、融点
103〜105℃のｐ−（ｐ−アセトオキシベンゾイル
オキシ）安息香酸ベンジルエステルの白色結晶が
得られる。Example 1 36 g of p-acetoxybenzoic acid and 71.4 g of thionyl chloride were charged into a 200 ml four-necked flask equipped with a condenser and a thermometer, and reacted at 50°C for 4 hours. Excess thionyl chloride is distilled off under reduced pressure to obtain p-acetoxybenzoic acid chloride. Next, 45.7 g of benzyl p-hydroxybenzoate, 20.2 g of triethylamine, and 100 ml of toluene were charged into a 300 ml four-necked flask similarly equipped with a condenser, thermometer, and dropping funnel. 30℃
and p-acetoxybenzoic acid chloride.
39.7g was dissolved in 50g of toluene, added dropwise over 1 hour, and then reacted at 50°C for 30 minutes. After cooling, the reaction solution was washed three times with 50 ml of water, and the solvent was distilled off under reduced pressure. When the residue is recrystallized from methanol, the melting point
White crystals of p-(p-acetoxybenzoyloxy)benzoic acid benzyl ester are obtained at 103-105°C.
Claims (1)
安息香酸ベンジルエステル1 p-(p-acetoxybenzoyloxy)
Benzoic acid benzyl ester
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5698684A JPS60199859A (en) | 1984-03-23 | 1984-03-23 | P-hydroxybenzoic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5698684A JPS60199859A (en) | 1984-03-23 | 1984-03-23 | P-hydroxybenzoic acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60199859A JPS60199859A (en) | 1985-10-09 |
| JPH043375B2 true JPH043375B2 (en) | 1992-01-23 |
Family
ID=13042813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5698684A Granted JPS60199859A (en) | 1984-03-23 | 1984-03-23 | P-hydroxybenzoic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60199859A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8925833D0 (en) * | 1989-11-15 | 1990-01-04 | Robertet Sa | Derivatives of aromatic benzoates as inhibitors of esterase-producing micro-organisms |
-
1984
- 1984-03-23 JP JP5698684A patent/JPS60199859A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60199859A (en) | 1985-10-09 |
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